Malononitrile compounds for controlling animal pests

A compound of formula (I) ,

• or a salt thereof, wherein
• Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R5;
• or naphthyl unsubstituted or substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R5;
• Q is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R6;
• C3-C8 cycloalkyl unsubstituted or substituted with one or more substituents R6;
• or C3-C8 cycloalkenyl unsubstituted or substituted with one or more substituents R6;
• R1 is hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R7;
• R2 is hydrogen or halogen;
• or
• R1 and R2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group;
• R3 is hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R7;
• R4 is hydrogen or halogen;
• or
• R3 and R4 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group;
• each R5, R6 is independently halogen, cyano, azido, nitro, —SCN, SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more Ra;
• C3-C8 cycloalkyl or C3-C8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more Rb;
• phenyl unsubstituted or substituted with up to 5 Rc;
• a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 Rd;
• Si(Re)3, ORf, SRf, OS(O)xRh, S(O)xRh, N(Ri)2, N(Ri)C(═O)Rm, OC(═O)Rm, C(═O)Rm, C(═O)ORf, C(═NRi)Rm, C(═S)Rm;
• or
• two R5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from CH2CH2CH2CH2, N═CH—CH═CH, CH═N—CH═CH, N═CH—N═CH, N═CH—CH═N, OCH2CH2CH2, OCH═CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH═CHCH2, CH2CH2O, CH═CHO, CH2OCH2, CH2C(═O)O, C(═O)OCH2, O(CH2)O, SCH2CH2CH2, SCH═CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH═CHS, CH2SCH2, CH2C(═S)S, C(═S)SCH2, S(CH2)S, CH2CH2NRK, CH2CH═N, CH═CH—NRK, OCH═N, SCH═N and form together with the carbon atoms the two R5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from ═O, OH, CH3, OCH3, halogen, halomethyl and halomethoxy;
• each R7 is independently halogen, cyano, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl, OSi(Re)3, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated;
• each Ra is independently halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C1-C6-alkyl-C3-C8-cycloalkyl, Si(Re)3, ORA, SRA, OSO2RB, S(O)xRB, —S(O)xN(RD)2, N(RD)2, C(═O)N(RD)2, C(═S)N(RD)2, C(═O)ORA,
• phenyl unsubstituted or substituted with up to 5 RE;
• a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 RE, or
• two Ra present on one carbon atom are together ═O, ═C(RF)2, ═NRD, ═NORA, ═NNRD, or
• two Ra form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two Ra are bonded to;
• each Rb is independently halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C1-C6-alkyl-C3-C8-cycloalkyl, Si(RG)3, ORH, SRH, OSO2RJ, S(O)xRJ, —S(O)xN(RK)2, N(RK)2, C(═O)N(RK)2, C(═S)N(RK)2, C(═O)ORH, or
• two Rb present on one carbon atom are together ═O, ═C(RL)2, ═NRK, ═NORH, ═NNRK, or
• two Rb form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two Rb are bonded to;
• each Rc is independently halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• Si(RG)3, ORH, SRH, OS(O)xRJ, S(O)xRJ, —S(O)xN(RK)2, N(RK)2, C(═O)RN, C(═O)ORH, C(═NRK)RN, C(═O)N(RK)2, C(═S)N(RK)2;
• each Rd is independently halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• Si(RG)3, ORH, SRH, OS(O)xRJ, S(O)xRJ, —S(O)xN(RK)2, N(RK)2, C(═O)RN, C(═O)ORH, C(═NRK)RN, C(═O)N(RK)2, C(═S)N(RK)2, or
• two Rd present on one atom of a saturated or partially unsaturated heterocyclic ring are together ═O, ═C(RL)2;
• ═NRK, ═NORH or ═NNRK;
• each Re is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C1-C6 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2;
• each Rf is independently hydrogen, cyano, C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• Si(Re)3, S(O)xRB, —S(O)xN(RD)2, N(RD)2, —N═C(RF)2, C(═O)RQ, C(═O)N(RD)2, C(═S)N(RD)2, C(═O)ORA, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2;
• each Rh is independently hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• N(RD)2, —N═C(RF)2, C(═O)RQ, C(═O)N(RD)2, C(═S)N(RD)2, C(═O)ORA, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2;
• each Ri is independently hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• S(O)xRB, —S(O)xN(RD)2,C(═O)Rs, C(═O)ORA, C(═O)N(RD)2, C(═S)Rs, C(═S)SRA, C(═S)N(RD)2, C(═NRD)Rs,
• phenyl unsubstituted or substituted with up to 5 RE;
• a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 RE, or
• two Ri on one nitrogen atom are together a C2-C7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl;
• each Rm is independently hydrogen, —SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more RM;
• Si(Re)3, ORA, SRA, OSO2RB, N(RD)2, C(═O)N(RD)2, C(═S)N(RD)2, C(═O)ORA, phenyl unsubstituted or substituted with up to 5 RE;
• a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 RE;
• each RA is independently hydrogen, cyano, C1-C6-alkylsulfinyl, C1-C6-alkyl sulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy and (C1-C6-alkoxy)carbonyl;
• each RB is independently hydrogen, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy and (C1-C6-alkoxy)carbonyl;
• each RD is independently hydrogen, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4-alkoxy;
• phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy and (C1-C6-alkoxy)carbonyl, or
• two RD on one nitrogen atom are together a C2-C6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• each RE is independently cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert -butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4-alkoxy, or
• two RE present on one atom of a saturated or partially unsaturated heterocyclic ring are together ═O, ═N(C1-C6-alkyl), ═NO(C1-C6-alkyl), ═CH(C1-C4-alkyl) or ═C(C1-C4-alkyl)C1-C4-alkyl;
• each RF is independently C1-C4 alkyl, C1-C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl;
• each RG is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 haloalkoxyalkyl;
• each RH is independently hydrogen, cyano, C1-C6-alkylsulfinyl, C1-C6-alkyl sulfonyl, trimethylsilyl, triethyl silyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• each RJ is independently hydrogen, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• each RK is independently hydrogen, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4-alkoxy;
• each RL is independently C1-C4 alkyl or C1-C4 alkoxyalkyl;
• each RM is independently halogen, cyano, azido, nitro, OH, SH, —SCN, SF5, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy, or
• two RM present on one carbon atom are together ═O, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)C1-C4-alkyl, ═N(C1-C6-alkyl) or ═NO(C1-C6-alkyl);
• each RN is independently hydrogen, OH, SH, —SCN, SF5, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• each RQ is independently hydrogen, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy and (C1-C6-alkoxy)carbonyl;
• each RS is independently hydrogen, OH, SH, —SCN, SF5, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
• phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)amino and di-(C1-C6-alkyl)amino;
• p is 0 or 1;
• x is 1 or 2;
• with the proviso that the following compounds are excluded:
• wherein R# is H, F, CN, with the proviso that not more than two R# are H.